A Long Weekend in Boston

This post is sponsored by BestBoston.com

Boston. Beantown. The City on a Hill.

Whatever you call it, if you haven’t visited this vibrant city, it should definitely be on your short list of U.S. cities to experience. A long weekend getaway is just enough time to see much of the best that Boston has to offer. When planning your trip you may find yourself a bit overwhelmed with all there is to do and see. However, with some careful planning you’ll be able to pack more in than you think possible.

When planning your weekend, be sure to note the opening and closing times for popular attractions. Certain attractions allow you to purchase tickets ahead of time, so be sure to take advantage of this so you don’t waste any of your weekend standing in line!

Five activities you can’t miss during your long weekend in Boston

The Freedom Trail

One of the awesome things about Boston is that you can visit many historic spots on foot! We love when cities are walkable and Boston is no exception.

The 2.5 mile long Freedom Trail is our number one can’t miss activity in Boston. You’ll have the opportunity to visit 15 historically significant sites, including the Paul Revere House and the USS Constitution. The walk is easy to do on your own as there is plenty of signage and information along the way. And we definitely recommend picking up a self-guided tour map from the Boston Common Visitor Information Center.

Now, if you’re a serious history buff or you’ve already done a self-guided tour of the trail, consider hiring a guide. Many of the guides are more than history buffs, they are actual historians! Finally, do some research ahead of time and pick out an interesting cafe or bar to stop at along the way. We suggest the Green Dragon Tavern and Museum for an extra dose of history.

The Prudential Skywalk

We love getting a birds eye view when visiting new cities. In Boston, the Prudential Skywalk offers this and more!

Take in the sights from above while listening to an informative audio guide (they even have a guide for kids!). The guide provides excellent historical information about Boston and points out specific landmarks and neighborhoods of interest. The guide makes the Prudential Skywalk the perfect place to kick off your weekend in Boston. You’ll leave with a great overview of the city and a better understanding of where everything is located.

And after enjoying the amazing 360 degree view, be sure to make a mental note to come back and catch the sunset.

Fenway Park

Fenway Park is home to the Boston Red Sox and perhaps some of the most loyal fans in all of North American sports! Take in “America’s Favorite Pastime” while enjoying the history of this 100+ year old stadium. Be sure to plan ahead to secure tickets for your specific dates as Fenway Park is always sold out.

If you’re visiting outside of baseball season or can’t find tickets, take part in an official tour of the stadium. Stadium tours are available year-round and offer plenty of photo opportunities, and you even get a chance to sit on top of The Green Monster. The guides are awesome and are seriously passionate about Fenway Park and the Boston Red Sox!

Seaport District

Popular for its waterfront seafood restaurants and bars, the Seaport District is one of the fastest growing neighborhoods in Boston. Make your way to this neighborhood for a high-end lunch or dinner at the Liberty Wharf while enjoying the beautiful seaside views. If beer is your thing, you can taste some local brews at the Harpoon Brewery and Beer Hall too!

If you’ve had your fill of food and drink by the time you arrive, take a stroll along the Harborwalk and simply enjoy this awesome part of Boston.

Mary Baker Eddy Library

I know what you’re thinking – A library? Really? But hear me out on this one.

The Mary Baker Eddy Library is home to original documents and educational exhibits about the life and achievements of Mary Baker Eddy. But a visit to this library isn’t complete without seeing the Mapparium. The Mapparium is a three-story stained glass globe that depicts the world as it was in 1935. It’s a great lesson in history and absolutely stunning to boot. Pictures don’t do this place justice, so you must see it for yourself. The tour guides even encourage you to test out the unique acoustics of the Mapparium by whispering and screaming!

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Meet Matt & Alana

Hello! We’re Matt and Alana, two Americans with a passion for traveling and experiencing new places. We are former full-time world travelers transitioning back to a U.S. way of life. Follow along as we figure out how to make the most of our vacation time and get the best bang for our buck in America and abroad!